Phenylacetic Acid → tert-butyl (2S)-2-[(Z)-N'-(2-phenylacetyl)oxycarbamimidoyl]piperidine-1-carboxylate

HRID 397645노트

반응식

HRID 397645 반응식
O.ON1C2C=CC=CC=2N=N1.[C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:41]/[C:42](=[N:56]\O)/[C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>CN(C)C1C=CN=CC=1.ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH2:56]/[C:42](=[N:41]\[O:20][C:19](=[O:21])[CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)/[C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]1[C:49]([O:51][C:52]([CH3:54])([CH3:53])[CH3:55])=[O:50]

참가 물질

9

반응물 5

HCID 999Phenylacetic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59085902tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

생성물 1

HCID 59085894tert-butyl (2S)-2-[(Z)-N'-(2-phenylacetyl)oxycarbamimidoyl]piperidine-1-carboxylate수율 91.3%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 311Citric Acid용매HCID 6344Dichloromethane용매2회

실험 절차

1-Hydroxybenzotriazole hydrate (8.67 g), phenylacetic acid (8.0 g), N-methylmorpholine (14.69 ml), 4-dimethylaminopyridine (3.3 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.29 g) were added to a solution of tert-butyl (Z)-(2S)-2-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate (13.0 g) [see Preparation 4] in dichloromethane (180 ml). The reaction mixture was stirred for 2 hours under an atmosphere of nitrogen, after which time the mixture was diluted with dichloromethane and 1N aqueous citric acid solution. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate and the solvent was removed under reduced pressure to afford tert-butyl (Z)-(2S)-2-(amino[(2-phenylacetyl)oxy]iminomethyl)-1-piperidinecarboxylate (17.63 g) as a white solid.

후처리

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-cec9c0ea11454573afd45b9294fbc604
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610707B1

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